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2017.04.03 13:37

[Thu. 6 Apr. 2017] Prof. Rong-Jie Chein/Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan

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Speaker Prof. Rong-Jie Chein
Date Thu. 6 Apr. 2017
Time 5:00pm
Venue #633, Asan Hall, College of Science

“Hydroxy/Amine-Directed Ortho-Alkylation and Its Application

in Total Synthesis of Panduratin D”

 

 

Hydroxyl/amine-directed ortho-nucleophilic acyl alkylations of N,N-diethylarylamides have been developed using a simple reagent combination of LDA and chlorosilane. The

transformations involve: 1) a complex-induced proximity effect (CIPE) in the deprotonation step, 2) an intramolecular Peterson-type reaction of the resulting α-silyl carbanion with the amide group, and 3) fission of the final β-oxygenated/nitrogenated silyl intermediate. The study of the mechanism, as well as the application of the protocol to an anionic Hellwinkel-Snieckus-Fries rearrangement, a series of highly efficient functional group transformations, and a total synthesis of Panduratin D, a cytotoxic natural product against pancreatic cancer cells, are reported.

 

 1.JPG

 

 

 

[1] H.-J. Lo, C.-Y. Lin, M.-C. Tseng, R.-J. Chein, Angew. Chem. Int. Ed. 2014, 53, 9026.

[2] C.-Y. Lin, M.-C. Tseng, R.-J. Chein, Synlett: SYNPACTS, 2014, 25, 2827–2830.

[3] I. F. Yu, R.-J. Chein, to be submitted.

[4] S. R. Bavikar, R.-J. Chein, to be submitted.

 

 

 

 

“Chiral Tetrahydrothiophene Ligands in Asymmetric Catalysis”

 

 

Chiral sulfur ligands are becoming a versatile tool in organic chemistry due to the

blossomed development achieved in the past years. This presentation describes an

expeditious and efficient preparation of enantiopure (thiolan-2-yl)diarylmethanols and

the applications of their derivatives to catalytic and asymmetric Corey-Chaykovsky

epoxidation,1 the imino Corey-Chaykovsky aziridination,2,3 as well as the first oxathiaborenium catalyzed asymmetric Diels-Alder reaction.4,5

 

2.JPG

 

 

 

Reference

1. Wu, H.-Y.; Chang, C.-W.; Chein, R.-J. J. Org. Chem. 2013, 78, 5788-5793.

2. Huang, M.-T.; H.-Y. Wu; Chein, R.-J. Chem. Commun. 2014, 50, 1101-1103.

3. Wang, S.-H.; Chein, R.-J. Tetrahedron, 2016, 72, 2607-2615.

4. Kumar, S. N.; Yu, I. F.; Chein, R.-J. Org. Lett. 2017, 19, 22-25. (Highlighted by C&EN 2017, 95(1), 9).

5. Tsai, M.-L.; Chein, R.-J. to be submitted.

 

 

 

Prof. Rong-Jie Chein

Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan


List of Articles
No. Subject Speaker Date
Notice Fall semester 2017 Seminar Schedule file - -
42 [Thu. 19 May. 2016] Prof. Zhuang Liu/Nanotechnology for enhanced cancer radiation therapy and immunotherapy Prof. Zhuang Liu Thursday 19 May 2016
41 [Thu. 6 Oct. 2016] Prof. Young S. Park/Atomistic Molecular Engineering of Polycyclic Aromatic Hydrocarbons Prof. Young S. Park Thursday 6 October 2016
40 [Thu. 9 Jun. 2016] Prof. Yong-Young Noh/Development of Printed Large Area Organic Transistors and Integrated Circuits Prof. Yong-Young Noh Thursday 9 June 2016
39 [Thu. 9 Mar. 2017] Prof. Woon Ju Song/Department of Chemistry, Seoul National University, Seoul, Korea Prof. Woon Ju Song Thu. 9 Mar. 2017
38 [Thu. 25 May. 2017] Prof. Wonsuk Kim/Department of Chemistry and Nano Science, Ewha Womans University, Seoul Prof. Wonsuk Kim Thu. 25 May. 2017
37 [Thu. 8 Jun. 2017] Prof. Won-jin Chung/Department of Chemistry, GIST, Gwangju, Republic of Korea Prof. Won-jin Chung Thu. 8 Jun. 2017
36 [Thu. 29 Sep. 2016] Prof. Tae-Young Yoon/Observation of Single Membrane Proteins under Mechanical Tension Prof. Tae-Young Yoon Thursday 29 September 2016
35 [Thu. 2 Jun. 2016] Prof. Sunkyu Han/Total Syntheses of Complex Alkaloids Inspired by Biosynthetic Hypotheses Prof. Sunkyu Han Thursday 2 June 2016
34 [Mon. 9 Jan. 2017] Prof. Sungwook Woo/Wyss Institute for Biologically Inspired Engineering, Harvard University, USA Prof. Sungwook Woo Mon. 9 Jan. 2017
33 [Thu. 26 Jun. 2016] Prof. Sung June Cho/Structural Elucidation of Novel Zeolite by Dual Space Approaches Using X-ray Powder Diffraction Prof. Sung June Cho Thursday 26 May 2016
32 [Thu. 17 Nov. 2016] Prof. Seunghoon Shin/Synthetic Methods Development based on Rational Analysis of Intermediates file Prof. Seunghoon Shin Thursday 17 November 2016
31 [Thu. 18 May. 2017] Student Host Colloquium : 1,1-Bisborylalkane: New Class of Organoboron Compound for the Chemo, Regio and Stereoselective Organic Transformations Prof. Seung Hwan Cho Thu. 18 May. 2017
30 [Thu. 23 Mar. 2017] Prof. Sangsu Bae/Department of Chemistry, Hanyang University, Seoul, South Korea Prof. Sangsu Bae Thu. 23 Mar. 2017
29 [Thu. 1 Dec. 2016] Prof. Sang-Yong Ju/Highly Pure Carbon Nanotubes sorted by a Flavin for Thin Film Transistor Applications Prof. Sang-Yong Ju Thursday 1 December 2016
» [Thu. 6 Apr. 2017] Prof. Rong-Jie Chein/Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan Prof. Rong-Jie Chein Thu. 6 Apr. 2017
27 [Thu. 3 Nov. 2016] Prof. Min-Sik Kim/Mass spectrometry and its applications to Biological Discovery Prof. Min-Sik Kim Thursday 3 November 2016
26 [Fri. 16 Jun. 2017] Prof. Martin Thuo/Department of Materials Science and Engineering, Iowa State University, USA Prof. Martin Thuo Fri. 16 Jun. 2017
25 [Mon. 16 Oct. 2017] Prof. Kirk S. Schanze/Department of Chemistry, University of Texas at San Antonio, Texas, USA Prof. Kirk S. Schanze Mon. 16 Oct. 2017
24 [Thu. 12 Oct. 2017] Student Host Colloquium : Versatile Dendrimer-Encapsulated Nanoparticles for Analytical Applications Prof. Joohoon Kim Thu. 12 Oct. 2017
23 [Thu. 1 Jun. 2017] Prof. Jong-Man Kim/Department of Chemical Engineering, Hanyang University, Seoul, Korea Prof. Jong-Man Kim Thu. 1 Jun. 2017
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